The Fear Of Settling
August 14, 2026
Adjusted for inflation, my current salary this year is almost exactly what I earned six years ago. Six more years of experience, a lot more skill, and the number hasn't moved an inch.
By the scoreboard I kept for most of my career, that's going backward.
It's also the freest I've ever felt about money, and it took me nearly twenty years in this business to be able to say that out loud.
Getting here cost more than it should have.
I talked myself out of the career I wanted over money
When I graduated high school, I knew what I wanted to do. I wanted to teach, and I wanted to coach baseball.
My own high school years hadn't given me much, and I had a real desire to help the next generation get more out of theirs than I got out of mine.
Halfway through college, I talked myself out of it.
The reason embarrasses me now. Teaching felt like settling. Our society counts success in dollars, and a teacher's salary doesn't add up to much.
So, somewhere in there I decided the version of me who wanted to coach kids wasn't ambitious enough, and that the guy I liked being wasn't enough to build a life on.
So, I built a different one. I added a business minor, went to graduate school for an MBA, then walked into investment management.
I didn't choose that field because I loved it. I chose it because it looked like the opposite of settling.
Why a good job stopped feeling like enough
Early on, I worked as an internal wholesaler at an asset management firm. Honestly, it was a good job. It was casual, low-stress, and it paid generously.
I carried none of the real risk.
But I couldn't stop looking one rung up. The external wholesaler I supported had the title I didn't: Regional Vice President. And he made more money than most doctors.
Next to that, my comfortable role looked small. If I stayed put, I told myself, maybe I just wasn't good enough.
So, I chased the rung.
I got the title and held it five years at a higher salary. But I never quite produced at the level required to run with the big dogs. That gap ate at me then.
Looking back, it's obvious why it was there.
I hated the job. I hated being away from my family. Most of all, I hated that my professional worth was measured by my ability to sell investment products I'd never put my own money into.
It's hard to be great at something when you don't believe in what you're working toward.
Years of misguided ambition eventually collected their bill. It came due as anxiety, then burnout, then a cancer diagnosis, all of which forced a transformation I hadn't gone looking for.
Out of it came a career change, from employee to entrepreneur, plus a promise that I'd never go back. For the first time, I was defining "more" on my own terms.
Then reality did what reality does. After several years of grinding to grow my income, the old voice came back with a new script: "What if I never get there?"
Why chasing more makes you like yourself less
Helga Dittmar and her colleagues at the University of Sussex, working with the psychologist Tim Kasser, pooled more than 250 separate samples of research on what happens to people who organize their lives around money and status.
Overall, the link between prioritizing money and feeling worse is real.
It’s what the researchers call negative self-appraisal. It isn't life satisfaction, which barely moves. It's self-doubt, and the nagging sense that you're failing to meet a standard you set for yourself.
There the effect runs two to three times stronger.
So, chasing the number doesn't necessarily make your life worse. What it does is make you think less of yourself, and that's a much harder thing to notice from the inside.
Their analysis points at why. A life built around money and image crowds out three things people need in order to feel well: having a say in how you spend your time, feeling like you're good at what you do, and being close to the people who matter.
Think about that for a minute. Which of the three is your job currently paying you to give up?
In the five years I was Regional Vice President, I had the title and the income, but none of those three. No say in how I spent my time. No belief I was good at the thing I was measured on. And I was almost never home.
More money was never going to fix any of that. But I kept reaching for it anyway.
None of this starts in adulthood, either. From the moment we arrive in Western culture, a quiet message starts playing in the background: you are not enough yet.
Not thin enough. Not rich enough. Not accomplished enough.
When Agnes Nairn and Suzanna Opree studied several hundred British schoolchildren, they found that greater exposure to advertising was linked to stronger materialistic beliefs. And that materialism, in turn, was tied to lower self-esteem.
We learn to feel behind before we’re even old enough to earn a paycheck.
So, if you've been saving carefully for years and still feel behind, you didn't invent that feeling. It got instilled early, usually before you were even aware of it.
Why I went back to a paycheck
Recently I took a W-2 role as a Senior Financial Advisor with Trek Wealth Solutions. That's the job paying me roughly what I earned six years ago.
And here’s the irony that I couldn’t have fathomed when I ditched that role: my new job gives me more freedom than entrepreneurship ever did.
I still prioritize my family over my work, but now there's a steady salary underneath it, which, with my wife's, gives our family more than we need.
That security buys something better than more money. It buys headspace.
And that headspace now goes into Reflective Wealth, which I converted from a wealth management company to a media and education company that I operate on the side.
It doesn’t really matter if it ever takes off. Because the work itself is the reward. I get to help others use money as a tool to live a more meaningful life, rather than as the measure of one. I get to help them define what enough looks like, so they can stop chasing someone else's notion of success and wealth.
The self I abandoned at 19, the one who wanted to teach and coach and help people get more out of their lives, was never the problem. That's the guy doing this work now.
I want to be careful with the word "settling," because for most of my life I used it as an insult, and it was the thing I was most afraid of doing.
But look at what I was actually afraid of. It wasn't a smaller life. It was a smaller number.
And that fear talked me out of the work I was built for and into jobs that cost me my health and my time with the people I love.
So, let me hand the word back to you without the sting I used to attach to it. What would you build if a good-enough income were a floor to stand on instead of a scoreboard to climb? And what would you finally have the nerve to try if failing just meant returning to a life that was already enough?
The freedom I was hunting at the top of the ladder had been sitting a few rungs down the whole time, in the decision to call what I had enough and spend the surplus on a life that was mine.
It might be waiting there for you, too.
Until next time, wishing you the best,
Bryan
Sources & further reading:
Nairn, A. & Opree, S. J. (2021). "TV adverts, materialism, and children's self-esteem: The role of socio-economic status."
Kasser, T. (2002). The High Price of Materialism.
Dittmar, H., Bond, R., Hurst, M., & Kasser, T. (2014). Meta-analysis of materialism and well-being.
Mullainathan, S. & Shafir, E. (2013). Scarcity: Why Having Too Little Means So Much.
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Not necessarily. Taking a job that pays less is only settling if money was the main thing that job was giving you, and for most people it isn't. A job also pays you in control over your calendar, in whether you believe in the work, and in how often you're home for dinner. None of that shows up on a W-2, which is exactly why it gets left out of the math. I spent five years as a Regional Vice President for the title and the income, and today I earn roughly what I did six years ago, with a say in how I spend my time and work I believe in. I'd make that trade again tomorrow. So the question isn't whether the number went down. It's what the bigger number was buying you, and what you were paying to keep it.
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More money stops feeling like more success because the standard you measure yourself against rises right alongside your income. Every new level quietly resets what counts as doing well, so the distance between where you are and where you think you ought to be never really closes. As an internal wholesaler I made good money and spent my days looking up at the Regional Vice President I supported. When I became the Regional Vice President, I spent five years looking up at the producers above me. I kept trying to close that distance, and it stayed almost exactly the same the whole time. That's why people who've won by every outside measure still describe themselves as behind. The scoreboard moves with you.
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Feeling behind after years of steady saving usually isn't about your balance at all. That feeling got instilled long before your savings existed, and it doesn't check your balance before it shows up. When Agnes Nairn and Suzanna Opree studied several hundred British schoolchildren for the International Journal of Market Research, they found the kids from the poorest backgrounds were both the most materialistic and the most vulnerable to what materialism does to a young person's self-esteem. The pressure to prove you're not settling lands hardest on the people with the least room to absorb it, and it starts early enough that most of us never notice we picked it up. So if
you've saved steadily for years and still feel behind, the saving is working. The anxiety riding alongside it just isn't telling you anything true about where you stand.
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Real ambition and fear of settling feel almost identical from the inside, and the way to tell them apart is to ask what you'd do the day after you got the thing you're chasing. Real ambition has an answer ready, something specific you'd build or try or make possible. Fear of settling has only relief, and the relief never arrives, because a new rung appears the moment you reach the one you were climbing toward. I chased a Regional Vice President title for exactly that reason, held it five years, and the relief never showed up once. So if you can't say what the promotion or the extra income would let you do differently, it's worth asking whether you're running toward something or just away from something else.
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No, and I'd push back on that reading pretty hard. Nothing here is an argument for earning less. Building your income and investing well are how you get a floor to stand on in the first place, and none of this works without them. I'm not saying money stops mattering. I'm saying money's job is to cover your life and buy you options, and once it's doing both of those, more of it stops delivering the thing you're chasing, which is usually the feeling that you're doing okay. The research says the same thing. Helga Dittmar and her colleagues at the University of Sussex pooled more than 250 samples and found the damage from prioritizing money concentrates in self-doubt rather than in your circumstances. Where that point sits is different for everybody, and working out where it sits for you is the whole exercise. In my experience it lands higher than the frugal crowd wants to admit, and lower than your ambition assumes.
